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Cheap flights from Chicago Midway Airport to San José from $220

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 8/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:20 am - 6:40 pm
MDW
-
SJO
11h 20m
2 stops
Southwest Logo
9:00 am - 9:50 pm
SJO
-
MDW
11h 50m
2 stops
$453Southwest
Wed, Aug 26 - Tue, Sep 1
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
$457Southwest
Mon, Sep 7 - Mon, Sep 14
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
Southwest Logo
9:00 am - 9:55 pm
SJO
-
MDW
11h 55m
2 stops
$461Southwest
Mon, Sep 7 - Mon, Sep 14
Delta Logo
6:00 am - 11:58 am
MDW
-
SJO
6h 58m
1 stop
Delta Logo
1:23 pm - 9:45 pm
SJO
-
MDW
7h 22m
1 stop
$482Delta
Tue, Oct 6 - Tue, Oct 20
Southwest Logo
10:30 am - 6:40 pm
MDW
-
SJO
9h 10m
1 stop
Southwest Logo
9:00 am - 5:40 pm
SJO
-
MDW
7h 40m
1 stop
$484Southwest
Wed, Aug 26 - Tue, Sep 1
Delta Logo
5:59 pm - 11:58 am
MDW
-
SJO
18h 59m
2 stops
Delta Logo
1:23 pm - 9:45 pm
SJO
-
MDW
7h 22m
1 stop
$487Delta
Mon, Oct 5 - Thu, Oct 22
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
Southwest Logo
9:00 am - 6:00 pm
SJO
-
MDW
8h 00m
1 stop
$490Southwest
Tue, Sep 8 - Thu, Sep 17
Southwest Logo
7:40 am - 6:40 pm
MDW
-
SJO
12h 00m
2 stops
Southwest Logo
9:00 am - 6:00 pm
SJO
-
MDW
8h 00m
1 stop
$494Southwest
Tue, Sep 8 - Thu, Sep 17
Southwest Logo
7:15 am - 12:45 pm
MDW
-
SJO
6h 30m
1 stop
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
$498Southwest
Thu, Sep 17 - Thu, Sep 24
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
Southwest Logo
9:00 am - 9:55 pm
SJO
-
MDW
11h 55m
2 stops
$501Southwest
Wed, Aug 19 - Sun, Aug 23

Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
Aug 26
MDW8:20 amChicago Midway
11h 20m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
Sep 1
SJO9:00 amSan José Juan Santamaria Intl
11h 50m
2 stops
MDW9:50 pmChicago Midway
$453
Southwest
Sep 7
MDW5:00 amChicago Midway
8h 45m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Sep 14
SJO9:00 amSan José Juan Santamaria Intl
11h 30m
1 stop
MDW9:30 pmChicago Midway
$457
Southwest
Sep 7
MDW5:00 amChicago Midway
8h 45m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Sep 14
SJO9:00 amSan José Juan Santamaria Intl
11h 55m
2 stops
MDW9:55 pmChicago Midway
$461

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Oct 6
MDW6:00 amChicago Midway
6h 58m
1 stop
SJO11:58 amSan José Juan Santamaria Intl
Oct 20
SJO1:23 pmSan José Juan Santamaria Intl
7h 22m
1 stop
MDW9:45 pmChicago Midway
$482
Delta
Oct 5
MDW5:59 pmChicago Midway
18h 59m
2 stops
SJO11:58 amSan José Juan Santamaria Intl
Oct 22
SJO1:23 pmSan José Juan Santamaria Intl
7h 22m
1 stop
MDW9:45 pmChicago Midway
$487
Delta
Aug 22
MDW6:05 amChicago Midway
6h 44m
1 stop
SJO11:49 amSan José Juan Santamaria Intl
Sep 28
SJO1:25 pmSan José Juan Santamaria Intl
7h 21m
1 stop
MDW9:46 pmChicago Midway
$502

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 24, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/26

8:20 am-6:40 pm

2 stops11h 20m

San José Juan Santamaria Intl

Tue 9/1

9:00 am-9:50 pm

2 stops11h 50m

$453

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/7

5:00 am-12:45 pm

1 stop8h 45m

San José Juan Santamaria Intl

Mon 9/14

9:00 am-9:30 pm

1 stop11h 30m

$457

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/7

5:00 am-12:45 pm

1 stop8h 45m

San José Juan Santamaria Intl

Mon 9/14

9:00 am-9:55 pm

2 stops11h 55m

$461
Quickest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 10/6

6:00 am-11:58 am

1 stop6h 58m

San José Juan Santamaria Intl

Tue 10/20

1:23 pm-9:45 pm

1 stop7h 22m

$482

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/26

10:30 am-6:40 pm

1 stop9h 10m

San José Juan Santamaria Intl

Tue 9/1

9:00 am-5:40 pm

1 stop7h 40m

$484

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 10/5

5:59 pm-11:58 am

2 stops18h 59m

San José Juan Santamaria Intl

Thu 10/22

1:23 pm-9:45 pm

1 stop7h 22m

$487

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/8

6:15 am-12:45 pm

1 stop7h 30m

San José Juan Santamaria Intl

Thu 9/17

9:00 am-6:00 pm

1 stop8h 00m

$490

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/8

7:40 am-6:40 pm

2 stops12h 00m

San José Juan Santamaria Intl

Thu 9/17

9:00 am-6:00 pm

1 stop8h 00m

$494

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 9/17

7:15 am-12:45 pm

1 stop6h 30m

San José Juan Santamaria Intl

Thu 9/24

9:00 am-9:30 pm

1 stop11h 30m

$498

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/19

10:10 am-6:40 pm

2 stops9h 30m

San José Juan Santamaria Intl

Sun 8/23

9:00 am-9:55 pm

2 stops11h 55m

$501

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $510. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $699. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $513. Flights at noon are often more expensive with an average ticket price of $680.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Fastest flight time

6h 44m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José takes 6h 44m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San José

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 44m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
7.9
4,270 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Santa Elena
Dominical
San Gerardo de Dota
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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